Enantioselective synthesis, crystal structure, and photophysical properties of a 1,1′-bitriphenylene-based sila[7]helicene

Koichi Murayama; Yasuaki Oike; Seiichi Furumi; Masayuki Takeuchi; Keiichi Noguchi; Ken Tanaka

doi:10.1002/ejoc.201403565

Enantioselective synthesis, crystal structure, and photophysical properties of a 1,1′-bitriphenylene-based sila[7]helicene

Koichi Murayama, Yasuaki Oike, Seiichi Furumi, Masayuki Takeuchi, Keiichi Noguchi, Ken Tanaka

Research output: Contribution to journal › Article › peer-review

30 Citations (Scopus)

Abstract

A 1,1′-bitriphenylene-based sila[7]helicene was synthesized with a high ee value by enantioselective double [2+2+2] cycloaddition of a biaryl-linked tetrayne with a silicon-linked bis(propargylic alcohol) as a key step. This sila[7]helicene exhibited a high tolerance toward racemization, which could be explained by the X-ray crystal structure analysis. With respect to the photophysical properties, this sila[7]helicene exhibited a relatively high fluorescence quantum yield and circularly polarized luminescence activity.

Original language	English
Pages (from-to)	1409-1414
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	7
DOIs	https://doi.org/10.1002/ejoc.201403565
Publication status	Published - 2015 Mar
Externally published	Yes

Keywords

Cycloaddition
Helicenes
Luminescence
Rhodium
Triphenylenes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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Enantioselective synthesis, crystal structure, and photophysical properties of a 1,1′-bitriphenylene-based sila[7]helicene. / Murayama, Koichi; Oike, Yasuaki; Furumi, Seiichi; Takeuchi, Masayuki; Noguchi, Keiichi; Tanaka, Ken.

In: European Journal of Organic Chemistry, Vol. 2015, No. 7, 03.2015, p. 1409-1414.

Research output: Contribution to journal › Article › peer-review

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abstract = "A 1,1′-bitriphenylene-based sila[7]helicene was synthesized with a high ee value by enantioselective double [2+2+2] cycloaddition of a biaryl-linked tetrayne with a silicon-linked bis(propargylic alcohol) as a key step. This sila[7]helicene exhibited a high tolerance toward racemization, which could be explained by the X-ray crystal structure analysis. With respect to the photophysical properties, this sila[7]helicene exhibited a relatively high fluorescence quantum yield and circularly polarized luminescence activity.",

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AU - Takeuchi, Masayuki

AU - Noguchi, Keiichi

AU - Tanaka, Ken

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Enantioselective synthesis, crystal structure, and photophysical properties of a 1,1′-bitriphenylene-based sila[7]helicene

Abstract

Keywords

ASJC Scopus subject areas

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